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How to Plan an Epic Off-Season Adventure

Rain, snow, or shine, here’s how to have a good time while off-season traveling—from packing tips to travel insurance

As the rain pricked my face, my smile couldn’t have been bigger. Nearly a dozen dolphins were zipping, zooming, and leaping just off the bow of our small overnight Fiordland National Park boat in New Zealand. While many guests ducked in and out of the downpour to see them, I stood there giddy, sans cover, oscillating between awe over the cetaceans and belly laughs with my equally rain-soaked husband.

The location, Milford Sound, a biodiverse yet notoriously rainy fjord on the South Island, may have been new to me, but the absurd elements that drenched us were definitely not. They’ve become my travel norm.

As an off- and shoulder-season traveler, weather-related misadventures are basically a given. I plan my globetrots outside of high season to avoid crowds, save money, and nab tough-to-obtain reservations—like my last-minute December 2023 booking for the Grand Canyon’s highly sought-after Phantom Ranch. Traveling in the off season can also benefit local communities. Since many destinations’ economies boom during the peak season, then wane beyond that, visiting in quieter times can provide more sustainable year-round income(Opens in a new window).

Plus, off-season travel—and the unpredictable weather it entails—can be a lot of fun. Instead of returning with a suitcase full of picture-perfect snapshots, I carry home packs upon packs full of epic stories. There’s the time I trudged through a snowstorm for a below-freezing camping trip on the Greenland Ice Sheet, then the downpour on a boat ride in Tahiti’s rainy season that had my husband and me in fits of giggles despite all of our belongings getting soaked. Or, most recently, our afternoons spent happily welcoming New Zealand’s spontaneous showers—knowing full well the treat of rainbows awaited us on the other side.

Sound fun? You bet it is! To help you plan your own shoulder- or off-season adventure, I’m sharing my tried-and-true tips, from what to pack to how to stay safe—and how to embrace the elements.

A landscape view of a foggy fjord
Image via Stephanie Vermillion

How to plan an epic off-season adventure


1.Pack for the weather

Traveling in high season typically comes with milder, and more predictable, weather. The off-season elements are a gamble—it could be rainy season without a drop of rain (which I experienced in Samoa in March 2024) or shoulder season with on-and-off showers (cough, New Zealand). No matter how the weather cards fall, the right gear will help you keep the adventures going rain, snow, or shine.

During our shoulder-season New Zealand adventure, we took Osprey’s new Downburst waterproof hiking pack(Opens in a new window) on every outing. It’s built like a backpacking pack, with sternum and waist straps, hip-belt pockets, and trekking pole loops, but the Downburst also integrates waterproof features that gave me serious peace of mind, especially with my expensive cameras. There’s an IPX5-rated waterproof main compartment, an internal zippered mesh pocket, and a top that can be rolled for maximum water resistance. The packs, available in 24L, 26L, 34L, and 36L, are also roomy enough to fit other off-season essentials like waterproof pants, a microfiber towel, and a GoPro camera to continue capturing the moment in a downpour.

If snow’s in the forecast, pack cold-weather garb that can withstand precipitation. Waterproof socks were particularly handy during my surprise-snowstorm camping trip on the Greenland Ice Sheet, as was my winter coat, hiking boots, thermal layer, and hand warmers. If you’re struggling to fit it all—trust me, I get it—try a compression sack(Opens in a new window) to condense the volume of your gear. 

A person walking on a boardwalk trail with mountains in the background and grasslands on either side
Image via Stephanie Vermillion

2. Optimize sunrise to sunset hours, and pack a headlamp

In some places, such as Iceland or Alaska, shoulder- or off-season travel comes with reduced daylight hours. This can shrink your adventure time, so it’s important to go into the trip knowing sunrise and sunset hours, then plan your excursions, and sleep schedule, accordingly.

In destinations where daylight dwindles quickly during the off-season, always keep a headlamp (and spare batteries) handy; that way you won’t be forced to turn around as dusk descends. Additionally, I like to adjust my sleep schedule around the sunrise and sunset hours so I can make the most of daylight. If the sun rises at 6 a.m., but sets at 6 p.m., I hit the hay early, then rise just before dawn. Sometimes I’ll even adopt the trip’s sleep schedule a few weeks in advance so my body gets used to it.

3. Research seasonal closures

Off- and shoulder-season travel isn’t all sunshine and rainbows—although New Zealand did have its fair share. In some destinations, particularly summer-centric getaways like beach escapes, restaurants, hotels, or tour operators close outside of peak season. That means main attractions may not be available or accessible.

If you have your heart set on a specific activity that’s only available during high season, you’ll obviously want to wait on the trip and choose a different destination. But, if you’re more flexible, a few closures here and there could actually be a good sign. Closed attractions often signals fewer crowds—and it could make popular adventures easier to book. Take that off-season trip to the Grand Canyon last December, where decreased visitation helped me snag a last-minute reservation for ever-popular Phantom Ranch, which typically books up over a year in advance. 

A rainbow over a fjord, with a grassy mountain in the background
Image via Stephanie Vermillion

4. Invest in travel insurance

Weather-related trip disruptions are part of the off-season gamble, especially in destinations that face issues like hurricanes, blizzards, or cyclones. That’s why travel insurance is a must. Travel insurance specifics varies by the plan you purchase; explore your options via comparison tools like Generally, insurance covers common issues like extended travel delays (such as being stuck in an airport) and cancelations due to bad weather. I typically use World Nomads, but other reputable travel insurance brands include Travel Guard and WorldTrips.

Some travel credit cards, such as those affiliated with an airline or the Chase Sapphire card, also include trip insurance that covers delays and cancelations. Coverage can often be more limited with these cards, so experts recommend buying additional insurance for long trips or those that cost over $10,000, according to Nerd Wallet(Opens in a new window).

5. Embrace the elements

Social media has created an expectation that globe-trotting will look as dreamy as it does on Instagram—but at the same time, Instagram is a highlight reel. Travel, even in the peak season, isn’t perfect. It’s unpredictable, that’s the fun of it, and off-season travel’s curveballs teach this lesson well. 

Go into your trip ready for it all: sunshine, downpours, or windstorms, or in places like dramatic Iceland, sometimes the mix of all three in one day. And most importantly, don’t forget to pack your sense of humor. A side of belly laughs can make even the dreariest day fun. 


Share your adventures with @ospreypacks